Former Mayor Maureen O’Connor was a mover and shaker in San Diego . . .
. . . until a shocking addiction to gambling took away everything she had.

Just before 10 a.m. Thursday, Maureen O’Connor made her way slowly, uncertainly into a small courtroom on the ground floor of the federal courthouse in downtown San Diego for what was going to be one of the more humiliating moments in her life. n The courtroom was just a few blocks from San Diego City Hall and the 11th-floor office that O’Connor occupied for 6½ years as the city’s first female mayor. n But the decline in O’Connor’s life between those heady days as mayor and her appearance as a defendant in a federal criminal case last week was far greater than the distance between the courthouse and City Hall.

Once vigorous and athletic, the products of a youth spent as an accomplished swimmer, the 66-year-old now uses a cane and tires easily.

Once articulate with a knack for math, she now has trouble at times following conversations, reading, even speaking, the remnants of a stroke following brain surgery.

And once wealthy, the beneficiary of a fortune estimated at $50 million left by her businessman husband, Robert O. Peterson, O’Connor is now virtually broke, the result of a stunning gambling addiction.

Her financial collapse is largely the product of years of gambling at casinos in San Diego, Las Vegas and Atlantic City. O’Connor — whose only known vice in her City Hall days was a penchant for Diet Pepsi — wagered more than $1 billion cumulatively over a nine-year span, most of it run up by spending hours at video poker machines.

Her net loss from the gambling came to an astonishing $13 million, her lawyer said.

Those mounting losses led in 2008 and 2009 to her taking $2 million from the charitable foundation established by her late husband, co-founder of the Jack In The Box restaurant chain, and using it to pay casino debts and continue gambling.

She has pleaded not guilty, but her case is on hold for two years in an agreement with the U.S. Attorney’s Office.

During that time, she will have to try to pay back the money, or as much as she can. She said last week she intends to do so and always did. She’ll also have to undergo counseling for gambling addiction.

The revelations shocked those who worked with O’Connor in her public life.

“It reminds me of a Shakespearean tragedy,” said Sal Giametta, chief of staff to county Supervisor Ron Roberts.

“You have this incredible rise, the prominence she had, and now to see something like this take place, it’s very disturbing,” said Giametta, who got his start in government as an O’Connor staffer.

Dad was a bookie

O’Connor was the eighth of 13 children in a Mission Hills Irish-Catholic family, headed by her boxer-turned-bookie father.

Her interest in politics was ignited after seeing what she thought was the poor treatment of Mexican Indians working at San Diego’s bicentennial celebration. Her complaints to the powers that be were ignored.

So O’Connor launched a grass-roots campaign for City Council, with her twin sister, Mavourneen, checking out a book from the library on how to run a campaign.

She won. The 25-year-old Catholic school gym teacher was the youngest to hold a council seat. Six years later, she wed Peterson, a financier 30 years her senior, in a small ceremony on the French Riviera.

Her initial 1983 mayoral campaign against county Supervisor Roger Hedgecock failed, but she later won when Hedgecock was forced to resign amid a campaign finance scandal. She took office in 1986, answering to the nickname, “Mayor Mo.”

She left behind a mixed bag of accomplishments and failures — and her share of critics and fans.

She knew how to play to the public, sometimes leading to criticism from those in City Hall about her lack of leadership and poor communication.

Her absences from meetings was a running joke, as insiders questioned what she did all day. She was also known to take in a midday matinee movie during the week.

She butted heads with the business interests and developed her image as a populist who met regularly with citizens, picked up trash with city crews, rode with police officers on patrol and walked tough neighborhoods.

She was applauded for her fierce fight against Southern California Edison’s takeover effort of San Diego Gas & Electric, which she won.

In one of her more memorable actions, O’Connor spent 48 hours as an undercover homeless woman, sleeping on the street, witnessing drug deals and prostitution, and experiencing firsthand how the city’s outreach programs worked.

She hid her famous face behind a ball cap and sunglasses, passing notable San Diegans on the street who didn’t recognize her as she walked the city on blistered feet.

At the end of her mayoral tenure, O’Connor largely receded from the public spotlight. She remained social, spending time with her close friends and her siblings.

Influential female friends

At one time, O’Connor was counted among the three most-powerful women in San Diego, along with philanthropist and McDonald’s heiress Joan Kroc and San Diego Union-Tribune Publisher Helen Copley. The three women frequently used their wealth and influence to frame the public conversation and partner on civic projects.

But they were also best friends, along with Oscar-winning actress Mercedes McCambridge, and privately bonded over their love of cinema and their shared Catholic values.

Copley and O’Connor enjoyed walks at La Jolla Shores, and the foursome would sometimes jet off in Kroc’s private plane or boat. They were some of the only women, besides a few nuns and her family, that O’Connor allowed to penetrate her small inner circle.

But by the end of 2004, within a span of only nine months, O’Connor’s tight circle shrank with the deaths of all three of her closest friends.

“Those were the women she identified with,” said Gerry Braun, a former San Diego Union-Tribune reporter who covered O’Connor as mayor. “Their loss I think is more important than people realize.”

The grief exacerbated a festering gambling addiction, one of her attorneys said last week.

Always considered a somewhat private person, O’Connor became more reclusive following her husband’s death in 1994, and especially so after her girlfriends passed. She relied on her close-knit group of siblings as her confidantes.

But Ben Dillingham, her former chief of staff, said that O’Connor did not completely withdraw. She just did her work out of the limelight.

“She loved to go out and help people, and she did it all very privately,” Dillingham said. “She was never the big party type. She didn’t go where she was likely to attract public attention.”

One of her recent outings was at a viewing for Copley’s son, David Copley, after his death in November. Those who attended said she seemed a bit frail but well.

Few had any inkling of what Eugene Iredale, O’Connor’s ﻿lawyer, described as her “lunatic” gambling compulsion.

“Complete surprise,” Giametta said.

Dillingham, who said he spoke with her on the phone often after she had a benign brain tumor removed in January 2011, said he knew that O’Connor gambled over the years but not excessively.

“I knew she gambled in the same way I knew that she liked to go to the movies,” he said.

She took private jets to casinos, where she went inside via a private entrance reserved for high rollers. She also went to local casinos, including the Barona Resort and Casino in Lakeside.

Her preferred game was a solitary one: video poker. She apparently played for hours at a time.

“Video poker is the crack cocaine of the business,” said Las Vegas gambling expert Stephen Gordon.

Video poker machines with maximum bets of $100 are common at casinos, and even $500 machines exist at some of the high-roller rooms.

That’s $1,000 for just two pops of the button. “It doesn’t take long,” Gordon said.

For O’Connor, it took about a decade to blow through her fortune, although medical records say her gambling habit began even earlier, after her husband’s death in the mid-1990s. Along the way, she sold homes, borrowed money from friends and liquidated savings.

She continues to receive an annual city pension of about $36,600.

O’Connor also has had serious health problems. After her brain surgery, she suffered a stroke. Iredale contended the tumor had been there for years and was in an area of the brain that controls decision-making and judgment. It could have contributed to her gambling compulsion, he said.

Federal prosecutors, who said O’Connor ran up her debts from 2000 to 2009, don’t agree.

Whatever the tumor caused, the operation left O’Connor physically diminished.

Booked and sent home

On Friday, O’Connor came downtown again to the federal courthouse. No cameras awaited her outside like the day before, when she entered her not guilty plea.

Iredale said she was tired but gratified by the support she had received over the past 24 hours. He said she was also embarrassed by her conduct.

She went to the basement, where the U.S. Marshals Service office is located. And then, the woman whose picture once appeared regularly on the front page of the U-T and who left a lasting imprint on the city as mayor, was formally booked into the federal prison system.

Marshals took her fingerprints. They took a booking photograph.

O’Connor was then free to go, back to the Mission Hills home she shares with her twin.